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I just spent a completely legal week in Cuba, split between Havana and Viñales. An American in Cuba in 2015 is a six part series on the trip. This post will focus on entry and exit requirements for Americans going to Cuba.

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Sunset Over Viñales, Cuba

Other Posts

Coming soon posts on booking flights to Cuba with miles or cash, money, internet, nightlife, lodging, transportation, Havana, and Viñales.


I’ve always wanted to go to Cuba because it’s there, specifically 90 miles from Miami, and I wasn’t allowed to.

Other reasons to go include the chance to see communism before it dies, pristine beach resorts, fine cigars and rum, to see crumbling 1950s beauty, and more chances for home stays with locals than in any other country I’ve visited.

Cigar Time inside a Barn Drying Tobacco
Cigar Time inside a Barn Drying Tobacco

The Current Rules for Americans to Enter Cuba

It has never been illegal for Americans to travel to Cuba, but it was illegal to spend money there without prior approval, and a trip there would be considered de facto proof that you had spent money there.

In January, President Obama announced a loosening of travel restrictions. Instead of having to have the Treasury Department certify that you are in one of the 12 approved categories for spending money in Cuba (ie travel to Cuba), you can self-certify with no advanced proof required. From the State Department’s website:

The U.S. Department of the Treasury’s Office of Foreign Assets Control (OFAC) has issued general licenses within the 12 categories of authorized travel for many travel-related transactions to, from, or within Cuba that previously required a specific license (i.e., an application and a case-by-case determination)… No further permission from OFAC is required to engage in transactions covered by a general license.

The 12 categories are:

  • family visits
  • official business of the U.S. government, foreign governments, and certain intergovernmental organizations
  • journalistic activity
  • professional research and professional meetings
  • educational activities
  • religious activities
  • public performances, clinics, workshops, athletic and other competitions, and exhibitions
  • support for the Cuban people
  • humanitarian projects
  • activities of private foundations or research or educational institutes
  • exportation, importation, or transmission of information or information materials
  • certain authorized export transactions

I went for journalistic activity, the product of which you are reading right now.

I’m not a lawyer, and nothing in this post should be considered legal advice, but, as a traveler, those categories look pretty broad to me. I’m sure anyone who wants to go to Cuba can find a way to plan a trip that involves a religious or educational activity. There are churches and schools all over the country. And, more importantly, I think the changes Obama announced sent a powerful signal to United States Customs and Border Protection (which he heads as the head of the Executive Branch) that they shouldn’t hassle people coming back from Cuba.

You must pick a category, and while I was never asked to prove my category before, during, or after my trip, I imagine it would be a good idea to have some supporting evidence at hand.

The Actual Steps and Paper Work Involved with Entering Cuba

Have ready for your trip:

  • Passport
  • Printed copies of your itinerary, especially your flight that leaves Cuba
  • Proof of Medical Insurance
  • Euros or Canadian Dollars (or less good, American Dollars, more on all this in a future post on money)
  • Evidence of which of the 12 categories you fall into

I checked in for my Copa flights from Washington DC to Panama City to Havana at Dulles Airport. (More on how to book flights in the next post; more on seeing the Panama Canal on my layover here.)

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Source: gcmap.com

Since I was on a one way ticket, the Copa agent asked me for proof of onward travel from Cuba. I showed her a PDF of my Asiana award from Havana to Bogota on my phone, which took me a few minutes to find. It would have been much easier to have brought a printed itinerary.

Screen Shot 2015-05-02 at 2.58.19 PM

She handed me this form in Spanish, presumably English copies are also available, which asked me to specify which of the 12 categories for a general license to travel to Cuba I fell into as well as some personal information.

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I completed the form and handed it back. I do not know whose form it is and whether the US government ever sees that form.

I was given both my Washington-to-Panama and Panama-to-Havana boarding passes by the agent, and I proceeded through security to my gate and a Chipotle burrito breakfast.

Other than that form and showing my flight out of Cuba, nothing was different about my airport experience at Dulles compared to what it would have been if I had been flying to Cleveland.

In Panama

In Panama City, as I was boarding the flight to Havana, I handed the agent my boarding pass and American passport. She handed me an equivalent form to the one I had gotten at check in at Dulles, but in English.

I completed that form and held onto it, and I was never asked for it at any point by anyone.

I asked her, “Don’t I need to get the Cuban visa here?,” and she said, “Oh yes!” You buy the Cuban visa from the airline for $20 cash.

Onboard I was handed the Cuban immigration form. Pictured below is the English form that asks which of the 12 categories I am (left), Cuban immigration form (top right), and Cuban visa (bottom right.)
Screen Shot 2015-05-02 at 2.59.03 PM

Upon arrival in Cuba, I proceeded to immigration. The agent needed my passport, Cuban immigration form, and Cuban visa.

I thought I was in the clear, but then she asked for proof of my medical insurance. I showed her my card that my American insurance company gives me. It is not travel insurance. She looked it over, and asked me, “This just says the number to call if you’re injured in Hawaii.” I pointed to an 800 number that said to call if injured elsewhere.

She accepted that, and gave me back my passport with half the Cuban visa. Do not lose that half of the visa. You need it to leave.

I’m pretty sure my medical insurance does not cover me in Cuba. I understand that Cuba sells travel insurance on the spot to tourists who arrive without proper proof of travel insurance. I have no first hand knowledge of that.

After immigration, there were a few tables of doctors (or nurses?) who appeared to be giving health checks.

Before you get to the doctors, grab a customs form.

The doctors stopped me, but when I showed my American passport I was let through without a check.

I had not checked a bag, so I proceeded past baggage claim to customs. I went into the “Nothing to Declare” line, and the agent asked for my customs form. Apparently I had missed it. It was right back after immigration. I went back, filled it out, and brought it back to the Nothing to Declare line where the agent made sure it was complete and then dropped it into something that looked like a ballot box.

I was free to leave the airport!

Key Points

  • Have passport, evidence of your category for Cuba travel (though this was never requested), evidence of flight out of Cuba, cash, and proof of medical insurance ready to go at check in
  • Buy a Cuban visa from your airline for $20 before you board your flight to Cuba
  • Get a Cuban immigration form on your flight to Cuba
  • Give passport, Cuban visa, Cuban immigration form, and proof of medical insurance to immigration agent in Cuba. Hold onto your half of the Cuban visa for exit.
  • Get a customs form after immigration and give it to customs agent after baggage claim

Leaving Cuba

Screen Shot 2015-05-04 at 12.50.59 AM
Among the Stalactites and Stalagmites of Santo Tomas Cavern

Things you need:

  • The half of the Cuban visa given back to you by the immigration officer
  • Your passport
  • 40-50 CUC (more on what a “CUC” is in the post on money)

A taxi from Vedado (a section of Havana, more on that in the Havana post) to the airport cost me 15 CUC, negotiated upfront. I believe you can negotiate a taxi from anywhere in Havana to the airport for 15 CUC, but if you are a bad negotiator or try to get a taxi outside of a hotel, be ready with 25 CUC.

The ride to the airport took about 30 minutes, and I got there almost about 2.5 hours before my flight. I almost never arrive more than 90 minutes before a flight, but I was glad I gave myself so much time. It took me 1 hour 26 minutes to get from my taxi to my gate.

I was flying Avianca to Bogota, and Avianca has another flight about 45 minutes earlier to San Salvador. The check in line was packed with people from both flights being checked in by four agents and no self check-in machines. It took me one hour from the start of the line to the end. The agent just needed my passport to check me in.

All other airlines had shorter check in lines for what it’s worth, but you may still want to arrive very early.

After getting your boarding pass, you have to pay the 25 CUC airport tax in cash. The line here was also very long, but the two agents could process people quickly, so I only waited about five minutes.

Next came emigration, which was hard to find because its entrance was blocked by so many Cubans who had come to the airport to see off their friends. The line here was another five minutes. I gave the agent my passport and the other half of my Cuban visa and got through quickly.

At no point during immigration or emigration was my passport stamped. I was hoping they would, but I didn’t ask.

Security took another few minutes, and I was at the gate about 60 minutes before my flight.

The airport does have WiFi. The only way to access it is with an ETECSA WiFi scratch card (more on all this in a post about internet), but none are sold at the airport as far as I can tell. If I had known this in advance, I would have brought one or two with me. There were also computers you could rent, but I didn’t have any more CUC or inquire about their price.

Key Things to Leave Cuba (Arrive very early)

  • Your passport
  • The half of the Cuban visa given back to you by the immigration officer
  • 15-25 CUC for your taxi
  • 25 CUC for your exit tax
  • ETECSA WiFi cards if you want to use the internet

Entering the United States

Global Entry Pitch

I have Global Entry, which means that I never have to fill out the United States paper immigration form and rarely have to speak to an immigration officer upon entering the country. If you have time to get Global Entry before Cuba, do it.

Global Entry saves me a few minutes to a few hours of time in line on every re-entry to the United States all for the cost of a $100 application fee, filling out a lengthy application, and one short interview with a Customs and Border Patrol agent. Plus Global Entry gets me TSA Precheck on all my domestic and international flights, which saves time and hassle when going through security. The $100 fee is totally worth it, but you don’t even have to pay that. Cards like the Citi Prestige® Card offer a $100 statement credit if you pay the application fee with your Citi Prestige. (My full review of the Citi Prestige.)

Entry into United States

After Cuba, I headed to Colombia for four days. This was in no way strategic; I just wanted to visit friends in Bogota. I flew back from Bogota to Miami to Washington DC. When I landed in Miami, I went through immigration. My kiosk experience was the same as always.

  • Scan my passport
  • Take a picture
  • Confirm my arriving flight
  • Answer “No” about bringing anything in that I needed to declare
  • Get my print out

I headed past baggage claim because I had no checked bags and handed my print out slip to the customs agent who waived me through.

Customs Rules

According to the US Customs and Border Protection website:

Can I import Cuban cigars into the U.S.?

Persons authorized to travel to Cuba may purchase alcohol and tobacco products while in Cuba for personal consumption while there. Authorized travelers may return to the United States with up to $100 worth of alcohol and/or tobacco products acquired in Cuba in accompanied baggage, for personal use only.

For further information, see this public notice from CPB.

I brought back about $50 worth of cigars.

What If You Don’t Have Global Entry?

My recollection is that the form that non-Global Entry folks fill out asks which countries you’ve visited on your time outside the United States. I would tell the truth, since if you’re in one of the 12 designated categories listed above, your trip was legal.

Bottom Line

Since January 2015, Americans can enter Cuba and spend money without prior approval of the Treasury Department as long as we self-certify that we are visiting Cuba for one of 12 permitted reasons.

Make sure you have everything you need for entry into Cuba, exit from Cuba, and entry back into the United States before making the trip.

The next post will focus on how Americans can buy flights to Cuba in 2015 with cash or frequent flyer miles.

Request for Comments

Cuba is a hard country to understand sometimes, and often I didn’t ask when I was confused because I didn’t want to draw attention to myself. Please comment on this and all future posts if you’ve been to Cuba. Did I make any mistakes or omissions? Did your experience differ? Your comments can really help people who are planning a trip to Cuba.

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Earn 50,000 bonus points (worth $800 in American Airlines flights) after spending $3,000 in the first three months on the Citi Prestige® Card. Plus get an additional $500 in free airfare on any airline in the first 12 months plus free airport lounge access worldwide for only a $450 annual fee. Why I got the card.


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I was just on the Rudy Maxa Radio Show discussing Round the World (RTW) trips since the end of Round the World awards.

My interview talked about how to book a huge RTW trip by piecing together underpriced awards. Here’s a master list of such awards:

To get the miles even for these cheap awards, you’ll need to get some credit cards.

Rudy mentioned signing up for my free newsletter.

Never miss a post again! Follow MileValue on Twitter and Facebook. And sign up to receive one free daily email every morning with all of the day’s posts!

Earn 50,000 bonus points (worth $800 in American Airlines flights) after spending $3,000 in the first three months on the Citi Prestige® Card. Plus get an additional $500 in free airfare on any airline in the first 12 months plus free airport lounge access worldwide for only a $450 annual fee. Why I got the card.


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You can very easily go to the Panama Canal at the Miraflores Locks on a multi-hour layover at Panama City’s Tocumen International Airport. You don’t even need to book a tour.

Screen Shot 2015-04-30 at 6.23.21 PM

Last week I used a 7.5 hour layover in Panama City on a trip from Washington DC to Havana, Cuba to visit the Panama Canal and see two ships moving through its locks en route to the Pacific Ocean. My whole excursion took about four hours from the airport back to it.

Why Go to the Panama Canal and Where Exactly Do You Go?

The Panama Canal is a wonder of engineering and human achievement. Ships are taken from sea level through three locks and other manmade and natural parts of the canal and then back to sea level in a different ocean. At locks, the ships are raised or lowered before moving through. Before the Panama Canal, to get around the Americas you had to go thousands of miles farther to the south of South America.

The nearest locks to the Tocumen Airport in Panama City are the Miraflores Locks, near the Pacific Ocean. These locks are 35 km from the airport and take 35 to 75 minutes of driving–depending on traffic–to reach. Here you can see ships going through the locks from an observation deck just a few dozen meters from the action, and you can tour the museum and Visitors Center.

How to Get to the Miraflores Locks

  1. Hire a taxi at the airport to take you to the locks, wait two hours, and take you back to the airport.
  2. Book a tour.

If you speak Spanish, the first option is definitely cheaper and preferable. Even if you don’t speak Spanish, you’re probably better off just booking a taxi when you arrive.

A quick search shows a tour that costs $107 for one person and charges extra for more passengers. I paid $60–Panama uses the US dollar–total for my taxi, and there would have been no extra charge for extra passengers.

Getting the $60 price took a little negotiating and a little walking around.

After exiting immigration (US passports do not need visa), there was a group of taxi drivers. I asked one what the charge would be to take me to the Miraflores Locks, wait two hours, and bring me back. He brought me over to the official desk, and they quoted me something crazy like $100. I walked outside and found some more taxi drivers. They offered me the trip for $90.

Then I saw one taxi driver alone. He offered me the trip for $60.

My theory is that the taxi company at the airport has a monopoly and exorbitant prices. Taxi drivers are unwilling to undercut the cartel if their co-workers are around. But if you find one alone, you can get a more reasonable price.

In the developing world, I think $60 is fair for 70 km of driving and four hours of the driver’s time. Maybe some drivers would be willing to go for less, but I can’t imagine getting cheaper than $50.

The taxi there at 2:15 PM took about 40 minutes. The taxi back at 5 PM hit rush hour traffic and took about 75 minutes, during which I mostly napped. Both ways, the drive gave great views of the coast and of Panama City.

The taxi driver stayed in the car for the entire two hours I was at the locks, so I left my carry ons in the car. Just in case he was some nefarious thief–he wasn’t–I snapped a picture of his license plate before going into the Visitors Center.

I am very glad I used a taxi instead of a tour for the money savings and convenience of going whenever I landed without having to make prior plans.

The Visitors Center at Miraflores Locks

Foreigners pay $15 for a ticket to the Visitors Center, which includes access to a few short films, a museum, and some rooms that recreate the view of engineers and ship captains during crossings.

First I watched a 10 minute film that runs nearly constantly alternating between Spanish and English about the construction and history of the canal.

Then I walked through displays about the construction of the museum. These were all edifying. They clarified to me who had built the canal, how difficult it had been, and why the United States eventually gave back control of the canal to Panama.

The museum featured a recreation of what engineers at the locks see…

Screen Shot 2015-04-30 at 6.22.14 PM

…and one of what ship captains see. I breezed through the film and museum in about 45 minutes. At that point I headed up the observation deck.

Here’s the view, which clearly shows the 54 feet a ship needs to be raised or lowered to pass the locks.Screen Shot 2015-04-30 at 6.22.24 PM

We were about to watch two ships that were being dropped down to sea level to head further south to the Pacific. There are two paths for the two ships to clear the locks simultaneously.
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When I arrived, the ships were just exiting the Pedro Miguel locks, just visible in the distance.Screen Shot 2015-04-30 at 6.22.42 PM

They trudged very slowly towards us, assisted by tug boats.Screen Shot 2015-04-30 at 6.22.52 PM

Dozens of us watched in rapt anticipation. Screen Shot 2015-04-30 at 6.23.13 PM

Finally the two ships arrived at the Miraflores Locks. A man over the loudspeaker–who basically emceed the afternoon–told us the nearer one was a Norwegian Cruise Liner and the farther one was a cargo ship.Screen Shot 2015-04-30 at 6.23.28 PM

At this point, the ships inch through the locks with only a few feet to spare and being guided by the small carts on the tracks on either side. The cruise liner had passengers on every deck.
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Finally the ships arrived at the point where they had to wait for water to be drained.

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And slowly the water did drain. Compare its level above and below.

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Unfortunately, it was now 5 PM. I’d been at the locks for two hours, and the museum closes at 5 PM, so I had to go. I didn’t quite get to see the ship pass through the locks completely, but I certainly got the idea.

I napped as my driver fought traffic back to Tocumen. We arrived at the airport at about 6:15 PM, I collected my bag, and handed him $60. My excursion was definitely worth $75 total since I don’t know if I’ll ever be back in Panama.

I already had my boarding pass for my flight to Havana–I had gotten it at check in in Washington–so I headed to emigration. After flipping through my passport, the person asked when I had entered Panama. I replied that I had just entered a few hours earlier and gone to the Canal. I think that’s why I had no stamp because I was just considered in transit. That satisfied the passport checker, and I headed through security and to my gate arriving about three hours before my flight.

My whole excursion took about four hours including traffic, so I think a trip to the Miraflores Locks is fine if you have a 5+ hour layover.

Bottom Line

Copa often offers the cheapest flights and best award space from the United States to South America, Central America, and the Caribbean via its Panama City hub. You can usually select a longer layover of up to 24 hours for no extra money or miles. If you have a 5+ hour layover, head to the Miraflores Locks to see an engineering marvel up close.

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Earn 50,000 bonus points (worth $800 in American Airlines flights) after spending $3,000 in the first three months on the Citi Prestige® Card. Plus get an additional $500 in free airfare on any airline in the first 12 months plus free airport lounge access worldwide for only a $450 annual fee. Why I got the card.


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My interview at Mint is up. I think it features better questions than most interviews I do.

Where do you see MileValue going in the next three years?

I have no idea.

I don’t make the rules of the rewards programs. Those are up to the airlines, hotels, and credit cards. I just figure out ways to maximize my and my readers’ benefits under those programs.

I know that no matter how the airlines, hotels, and banks construct their loyalty programs, there will be ways to get out-sized rewards; and I will continue to uncover and share those ways so everyone can travel more, better, and cheaper.

Click the link to check out my answers to other questions like my three tips to individuals looking to earn miles and travel without breaking the bank.


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Registration for the 2015 Chicago Seminars is now live as of noon ET. Click here to register. As in past years, it costs $100 and there are 500 spots.

The seminars will take place from 5 PM on Friday October 16 until 4 PM on Sunday October 18 at the Holiday Inn Chicago — Elk Grove, which is NOT in the city but near O’Hare. That’s convenient for 4,500 to 7,500 Avios flights from much of the country.

I will be speaking at the Seminars. The topic is to be determined, but you can bet it will have to do with redeeming miles. Here are the slides from my two presentations last year on The Southwest Companion Pass and Trick Awards.

The event and the hotel will sell out–already 70 spots are gone in the first 20 minutes. I recommend booking both as soon as possible if you want to attend. (Not staying at the hotel will be a lot less fun.)

Here’s a thread about last year’s Chicago Seminars to let you know what to expect. What I expect is meeting a lot of you, impromptu dinners and drinks to which everyone standing in the lobby is invited, and learning a few new things from presentations.

I leave you with this gem from my first Chicago Seminars in 2012, with Mommy Points.

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Every time you use your credit card, the bank is earning swipe fees from the merchant. It’s these swipe fees plus other ways that banks profit off credit cards–interest fees, late fees, advertising to cardholders–that pay for the perks we get from credit cards.

How much of these fees are rebated to us? According to a recent article in The Economist:

[C]ard issuers are providing bigger rebates on purchases, more frequent-flyer miles as a sign-up bonus and longer interest-free periods for those who transfer balances from other cards. Mercator Advisory Group, a consultancy, estimates that the amount of revenue from each transaction passed back to the customer has been growing for years. In 2012 it put it at 47% for three of the biggest issuers, up from 39% in 2010.

According to the Mercator Advisory Group (according to The Economist) we got back 47% of the revenue from each transaction three years ago. Unfortunately I couldn’t find the underlying study or press release anywhere online by googling all the relevant keywords. If you can, please post a link in the comments.

I get back a lot more than 47% of the swipe fees the bank collects on me. So much of my spending is going toward clearing sign up bonuses and maximizing category bonuses, that I definitely average more than 3 miles per dollar across all my spending. Even assuming credit card companies can buy miles for 1 cent each (I don’t think they get them that cheaply), that works out to costing credit card companies at least 3% of my purchases in rewards. There’s no way they are making that back off swipe fees (or any other fees, since I don’t ever pay interest.)

Of course, there’s nothing average about the way I approach credit cards.


One other interesting chart from the article:

Screen Shot 2015-03-03 at 4.52.28 PM
from The Economist


Ignore the red line and focus on the blue bars, which show that the average bonus miles offered on new cards rose from about 9,000 in 2011 to about 14,000 in 2015.

What? Huh? What?

The only time I see an airline card with such a putrid bonus is the 10,000 mile offer on the JetBlue card. Every other airline card offers 25,000, 30,000, 40,000, or 50,000 miles (like on the American Airlines card at the moment.) And sometimes airline bonuses hit as high as 100,000 miles like on the American Airlines Executive card last year.

The only possible way to get such tiny averages (9,000 and 14,000) is if the calculation includes all credit cards, many of which come with zero bonus. That’s a weird way to construct the average: averaging in a bunch of zeros.

Bottom line: it’s always fascinating for me to read the mainstream media on credit cards and miles because, on the one hand, they have better access to certain data and can do more research, and on the other hand, they don’t get it.



I earn a commission for some links on this blog. Citi is a MileValue partner.

Are you sick of missing out on mistake fares, mistake rates on hotels, and other limited-time offers that you didn’t hear about in time?

Here’s the brand new solution:

I’ve created a new Twitter account, @MileValueAlerts, that I’ll only use for huge deals you need to know about right now before it’s too late. The account is designed to be subscribed to by SMS, so on the rare occasions I use the account, you get a text message instantly.

You’ll never miss another mistake fare.

How rarely will I tweet from the account? Here are the four most recent tweets I think I would have made.

That’s four tweets in the last two months.

Because I will almost never tweet from the account, you can safely set up your Twitter account to send you a text message when I do post without fear of getting many text messages.

(I will continue to post multiple times per day on the normal @MileValue twitter account, including mistake fares as they arise, but @MileValueAlerts will be dedicated to mistake fares and the impending demise of similar offers.)

How to Set Up Your Twitter Account to Text You Every Time @MileValueAlerts Posts in Three Easy Steps

Step 1: Add your mobile number to your Twitter account

Click your image in the top right of any Twitter screen and select Settings.

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Select Mobile from the menu on the left.

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Add your number and confirm the code texted to you.Screen Shot 2015-02-19 at 5.01.50 PMStep 2: Turn on SMS Notifications

Under the exact same Mobile Settings tab you went to in Step 1, look for the area labeled “Text Notifications.” Check the box for “Tweets from people you’ve enabled for mobile notifications.”

Step 3: Add @MileValueAlerts Alerts

Go to @MileValueAlerts Twitter page. Follow it. Next to the button that says Following, click the gear icon and select “Turn on mobile notifications.”

Screen Shot 2015-02-20 at 10.51.24 AM

Now you’re set up to receive a text message every time @MileValueAlerts tweets. You can, of course, follow the same process to add other accounts for text message alerts, but I personally don’t want to get a text every time any regular Twitter user tweets.

Bottom Line

I used to be super bummed when I’d miss a mistake fare. Now you won’t have to miss any more. You won’t need to be by Twitter or on a blog when a deal blows up. You’ll just need to be with your phone (and who isn’t chained to that?)

The second I tweet the deal from my brand new account @MileValueAlerts, you will be texted. Sign up for text message alerts from @MileValueAlerts with confidence. I will only use the account for the biggest deals you need to know about right now because their death seems imminent.

Never miss a post again! Follow MileValue on Twitter and Facebook. And sign up to receive one free daily email every morning with all of the day’s posts!

Meeting the minimum spending requirement on the Arrival Plus give you about $500 worth of free flights on any airline with no blackouts.

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Last month, the new design of milevalue.com went live, and I walked through some of the changes in “MileValue Looks Different.”

The team behind the design was Third Harbor, specifically Tyler and Emily.

Tyler has a lot of experience in the field, but this specific company is new, and he was too busy working on several client projects to get his own website up until now. This is how Tyler explained to me what Third Harbor is:

My new company is called ‘Third Harbor’ (http://www.thirdharbor.com). We help non-technical founders plan, develop, and launch technical projects, apps, companies, and websites. Our work largely falls into three categories: design and development, Minimum Viable Product creation, and web presence management.

In addition to our roles as designers and developers, we also function much like a film producer. We manage the needs of each project as they arise, and save our clients the trouble of finding, vetting, and managing individual contractors.

That’s me. A non-technical founder.

I’m putting this post out to get as free advertisement for Third Harbor because I am happy with their work.

I’m happy with how MileValue looks, really happy with the level of responsiveness during the planning stages, transition, and putting out post-transition fires. I definitely recommend Third Harbor to anyone.

Tyler and I started with my ideas, and he figured out how to implement them. Third Harbor can do the same for you.


I earn a commission for some links on this blog. Citi is a MileValue partner.

I looked back on my 2014 travels on New Year’s Eve, and I want to share my 2015 travel goals today. More importantly, I want to explain how you can turn your 2015 travel goals into reality by taking the first baby steps toward your dream trip today.

My Plan

I have a general idea that I am in the middle of about a nine month trip that will follow summer from South America to Europe.

Right now I am in Chile, trekking Torres del Paine. In a few days, I’ll move on to El Calafate and El Chalten, Argentina before ending my Patagonia trip with a flight back to Buenos Aires.

I expect to stay in Buenos Aires until mid-March when I will head to the United States to follow the University of Virginia’s basketball team through the ACC and NCAA tournaments. I did this last year, and it was so much fun that I couldn’t pass up the chance to do it again. In between games, I like to visit friends and family around the east coast.

In early April, I want to head to Sevilla, Spain for one month (possibly with some A380 First Class flying and a stop in the Middle East along the way.)

I don’t have this next part totally worked out, but I think I want to live one month in a city in the Balkans and then one month in a city in the Baltics, possibly with some travel in those regions in between. I will need to be mindful of spending less than three months in the Schengen Area, though that shouldn’t be too hard since most of the Balkans are outside the Schengen Area. It is nice that the euro is down to $1.22, which is the lowest it has been in years.

This plan puts me in Europe until July or so, at which point I will probably return to the United States, but that’s so many months and countries away that my foresight is getting very blurry.

Here’s my best guess for countries I will hit in 2015. It’s fewer than in years past with nothing east of the United Arab Emirates in mind.

Screen Shot 2014-12-29 at 9.25.35 PM
from amcharts.com

How You Can Reach Your Travel Goals in 2015

  1. Pick a place you’d like to travel to in July 2015 or later (so you have time to amass miles), who you want to go with, what cabin you want to fly, and what lodging you want.
  2. Fill out my Free Credit Card Consultation Form, so I can help you collect the right miles for your goal or let you know the goal is unattainable. If instead you collect miles at random, you will probably collect the wrong miles for the job.
  3. While you are collecting miles, read MileValue posts on how to use the miles you’re collecting. Start with the posts on the basics of all the major programs in the Free First Class Next Month beginners series.
  4. Once the miles post, book your dream trip.
  5. Or skip steps 3 and 4, and hire the MileValue Award Booking Service when your miles post.

Your Turn

In the comments, share your travel goals for 2015 to put yourself on record (just stating a goal makes you more likely to accomplish it) and to inspire us. I’m not above stealing good ideas, so if your plans sound better than mine, I just might change my plans.

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I earn a commission for some links on this blog. Citi is a MileValue partner.

2014 was a great year of travel for me, and hopefully for you too.

Last year (2013) was a year of deep and broad travel since I spent almost six months in Argentina and another two months flying through 21 total countries. I spent over nine months outside the United States

This year (2014) was focused on three main trips with much more time spent at my home base on Oahu:

  1. Fly the best First Classes / see SE Asia / follow UVA basketball through the ACC and NCAA tournaments.
  2. World Cup
  3. Start of a nine month trip to follow Summer through South America and Europe (next summer.)


Screen Shot 2014-12-29 at 9.21.38 PM
from amcharts.com

In chronological order (excluding countries where I never left the airport):

  • United States (9 months; Hawaii: 7.5 months; mainland: 1.5 months)
  • Macau (1 day)
  • Singapore (4 days)
  • Cambodia (8 days)
  • United Kingdom (2 days)
  • Slovenia (4 days)
  • Brazil (10 days)
  • Hong Kong (4 days)
  • China (3 days)
  • South Korea (5 days)
  • North Korea (2 minutes)
  • Colombia (28 days)
  • Argentina (24 days)
  • Chile (5 days)

All of these countries were new except the United States, United Kingdom, and Argentina. My total is now 55 (counting England, Wales, Macau, Hong Kong, and China separately):

Screen Shot 2014-12-29 at 9.19.07 PM


In chronological order (with links to trip reports):

Unfortunately six of these premium cabins were the front of United planes, which are comfortable but not exactly luxurious.

My favorite flights were in Cathay Pacific First Class and Asiana First Class.

MILES FLOWN (88,392)

  • 88,392 miles flown over 45 segments
  • If I had flown all these as paid flights on one airline like United or American, I wouldn’t even have top tier status!
  • Longest flight: JFK to Hong Kong in Cathay Pacific First Class (8,072 miles)
  • Shortest flight: Honolulu to Kahului, Maui (100 miles)
  • Favorite flight: JFK to Hong Kong in Cathay Pacific First Class. 16 hours wasn’t long enough
  • Runner up: Puerto Williams to Punta Arenas, Chile in the front row over the mountains, fjords, and oceans of Patagonia with a view of the cockpit

Screen Shot 2014-12-27 at 10.16.38 AM



  • Biking the walls of Angkor Thom in Cambodia.
  • Jumping into the FREEZING cold Beagle Channel in Puerto Williams, Chile
  • Trekking 4 days in Torres del Paine National Park, Chile
  • Watching the last few minutes of the United States loss to Belgium in the World Cup as we mounted a frantic comeback surrounded by Americans and Brazilians at the FIFA Fan Zone in Sao Paulo.
  • Playing two USTA National Championship tournaments in Palm Springs, CA and Tucson, AZ with great friends from Hawaii.
  • Celebrating at the Obelisk in downtown Buenos Aires when River Plate won the Copa Sudamericana soccer tournament.
  • Being at all three UVA games at the first ACC tournament we’ve won since 1976. Being at all three NCAA tournament games including the Sweet 16 loss at Madison Square Garden with my brother.
  • Haircuts and a shave in Medellin, Colombia and the Indian section of Singapore.
  • Cliff jumping from 30 feet at several spots on Oahu and Maui.
  • Flying a friend to Oahu and Maui with Avios to spend a week together.
  • The nightlife-turning-into-daylife in Sao Paulo, Rio, Bogota, Medellin, and Buenos Aires.
  • Hiking the Great Wall of China with my brother.
  • A bike tour of rural livelihoods in Battambang, Cambodia.
  • The DMZ between North and South Korea.
  • Hiking to Sai Wan in Hong Kong and discovering a beautiful beach and natural pool.
  • Meeting new friends along the way.
  • Reconnecting with old friends from previous trips.
  • Visiting family.

Upon reading the list, I’m struck by how idiosyncratic my favorite moments were. Surely most of my readers wouldn’t have enjoyed many of my favorite moments. What’s great about miles is that they work for you to make your dream trips happen. They are not one size fits all. We can all be a part of the same community even though we have wildly different travel styles and goals.

What were your travel stats for 2014? More importantly, what were your best travel memories from this year?

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Merry Christmas from Ushuaia, Argentina.

Screen Shot 2014-12-25 at 12.47.29 AM
from Google Maps, not too far from Antarctica

I just had the pleasure of delivering presents at midnight in full Papá Noel (Santa Claus) suit to the hostel owners’ excited 1-10 year old kids. I should have pictures soon, but I was too busy ho-ho-hoing to snap any. I hope your Christmas is as fun as that.

As I did for Thanksgiving, I’ll take off until Sunday because who reads about miles and points during their 5-6 day weekend? Here are some recent interesting posts if you want to brush up on anything you have missed.

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The Washington Post has an interesting poll running right now. It’s really just one question about what you call the commercial airport closest to DC.

Screen Shot 2014-12-15 at 12.06.06 PM

Beneath that, there are several demographic questions that I’m sure they’ll try to correlate your answer like how old you are, where you grew up, and how often you fly out of that airport that we’re trying to figure out what to call.

Screen Shot 2014-12-15 at 12.06.16 PM

I grew up in Fredericksburg, VA, which is about equidistant from said airport, Dulles, and Richmond International Airport. I mainly have flown out of Dulles because it’s a United hub and because I have cousins just a few minutes from the airport.

I answered that I call the other airport “National.” I’m fairly consistent about that though if I’m writing to an audience that knows the airports, I’ll usually write “DCA.”

What do you call that other airport in Northern Virginia that isn’t Dulles?

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I gave a well-received presentation on Trick Awards at the Chicago Seminars in October.

The presentation dealt with free one ways, negative price one ways, open jaws, stopovers, avoiding fuel surcharges, and award chart SUPER sweet spots.


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I earn a commission for some links on this blog. Citi is a MileValue partner.

In October, I had the pleasure of speaking at the Chicago Seminars. My original slot was to speak about Trick Awards, but a last minute cancellation by another speaker had me also speak about the Southwest Companion Pass.

Here are my slides from the presentation, which are another way to consume the information in this post: Southwest 50k Offers Are Back, Leverage Them for $3,142 in Free Flights.

The presentation also contains some of my best tips about Southwest like how to snag the best seats, when Southwest’s ticket prices go up (this is pretty regular in my experience, and much more.

Also see Free Giveaway: $51 Southwest Gift Card.

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After 2.5 years, I finally spruced the place up a little bit. Thanks to Million Mile Secrets for letting me steal his theme for a few years, but now I’ve got my own. ;)

Almost all the changes are cosmetic. Let me walk you through a few of them.

First, you probably noticed that you got a pop up when you came to the site today. Sorry for the minor annoyance. I just really want people to sign up to receive one free daily email every morning with all of the day’s posts! You will see this pop up no more than once per month.

Next, the home page has seen a total redesign.

Screen Shot 2014-12-11 at 3.20.18 AM

For anyone who stumbled onto the site not knowing where they are, we’ve added a prominent button to Start Here. Underneath it, I’ve added a few of the top credit card offers. Before they lined the sides of the page, but I don’t want people to confuse them with randomly generated ads. These are handpicked offers.

Next comes all the posts. I wanted to fit a lot more posts onto the home page, so great content that’s only a week old isn’t hard to find.

Post pages look a little different than before, and offer you the chance to share a post you think your friends will find helpful with just the click of a button at the bottom of the page.

Screen Shot 2014-12-11 at 3.26.00 AM

The key services of this site: the blog, the Award Booking Service, and the Free Credit Card Consultation remain the same.

Hopefully you like the makeover. Big shoutout to Tyler and Emily for the design work. For anyone who has a website, I’ll give a little more info on their company in a few days. They’ve worked so hard on my site that they haven’t finished their own!

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